Boss Ch. 03

The next morning dawned like those before it, except I felt this mash of total anxiety and deep relaxation racing back and forth across my lower abdomen.

As I stretched my body and awoke, I inched my fingers down across my belly to the tuft of public hair and ran my fingers down until they finally gripped and warmed themselves on my penis.

As I gently squeezed myself there in bed I started to go through the scenarios again, pumping and kneading myself with my fist. I remembered the first time with Anne, my boss, at the local advertising agency, of me sitting there, buck naked, slurping on her hot labia in the office. Then I flashed forward to her warm mouth sucking my hunkering dick the night before, drinking my cum, telling me I was well-hung and beautiful.

She also told me another interesting fact I recalled as I lay there masturbating myself before work. We'd be getting an intern and I was supposed to "train" her. After being given this assignment from my superior after a bout of deep oral sex, I thought that "train" had other connotations, but did it?

Anne said she was a 19 year old kid who wanted to get into advertising. Her name, I remembered, was "Allison." Almost automatically I envisioned her walking into the office. She would be wearing casual blue jeans and maybe a tank top (it was still early autumn) and she would have blue eyes and an auburn pony tail. Pulled back. Perfect for gripping and using as she descended on my organ - all at Anne's request, of course.

The idea of having a "hot young co-ed" promised to me really turned me on and so it wasn't long before my hips bucked and I shot off a dry load. I was still empty after the night with Anne. And soon I would have to face her again.

****

As I pulled my clothing on and headed towards work in my car I felt oddly at ease. I was listening to some pretty chill music and I had already emptied my tank, so I felt quite confident striding into the office to face Anne. But the first person I bumped into was Barbara, our really big superior. The one who had an office, but where it exactly was located I couldn't tell.

Barbara was medium height with curly chocolate brown hair. She was Italian or Greek American, and she had olive oil skin, that was aging healthily. She must have been about 46 or 47. She liked to wear small silver hoop earrings, and she always had her nails done. She also liked to wear a black sporty leather jacket, and curl her hair as she talked to an important customer. She was buxom and filled in nicely for a middle aged woman. If Anne was the brains behind our agency. Barbara was definitely the face and she had a face that I would do.

"Hi Peter, How are you?" she asked with a buoyant smile.

"Oh, I feel great, Barb," I shot back.

"Oh, I bet you do," Barbara replied with a bit of mischief. "I bet you do."

I paid no mind. I had no illusions that Anne would keep her lips sealed the night after they were so open and extended around my young dick. It was natural for her to flaunt her sexual prowess. I'm sure I would be telling my buds all the details once I got back to school.

"So what's up Barb?" I asked trying to get off the very sensitive topic.

"Well, today is the day you are promoted," she said. "You have an intern coming in at noon and I expect you are knowledgeable enough to show her the ropes, especially during a busy week like this week," Barbara said.

"So just remember to be polite. And be professional," Barbara said. Just then her hyperactive mobile phone acted up and rang. "Oh, I gotta take this," Barb said. "Talk to you later, Peter."

"Be professional. Bet you know." I know that it may be normal that the older ladies at the firm I worked at might share, but I kind of felt a little strange about figuring it out for myself in the parking lot. With the head honcho no less.

Shaking our conversation off I strode into the office, and then downstairs past Anne's office, where she sat there, her usual self, the computer screen light fogging up her glasses.

"Hi Peter," she said in a business-like way. "Today is the day Allison is coming in so I want you to put her an introductory folder together."

"OK Anne" I said, enjoying the thrilling game we were playing. "Where's the stuff for her folder?" I asked. "It's in the back" she replied. "I'll be back there in five minutes to give you some more feedback on it. Just go ahead on back."

I walked into the backroom and took a look at the documents lying on the table, which sort of chronicled what kind of menial tasks this poor girl would have to do under my supervision. Believe me it was going to be a boring internship for 19-year old Allison Co-Ed. She might even get so bored that she...

I heard the door close behind me.

"Hi Peter," said Anne. "Hi," I responded coldly.

"So you want to know about your new assignment?"

"Yes," I said, feeling more apprehensive.

I was bent halfway over the desk with the papers and Anne walked up slowly from behind, placing one of her hands on the small of my back, and the other hand around my waist, right above my belt.

"Well," Anne said, as she began to slowly massage me in these two sensitive places, "your assignment is named Allison."

"I know," I said sarcastically. I felt like James Bond as played by Sean Connery, simultaneously making love and trying to get more information out of this very potent adversary.

"And it is your job to train her," she said. She then started slipping her hand down below my belt, connecting with the tip of my warm and growing cock.

"Oooh," she said. "What have we here? I remember this thing," she said, undoing my belt buckle and button. Slowly she let my cock out of my pants and held it in her warm palm.

"This is the young cock I had in my mouth last night, isn't it?" she said gripping me tightly. Her other hand lowered from my back and clasped my balls, her finger nails gently scraping and playing with them. Something had come over Anne. She was much more direct and more empowered since she had gotten laid. I wonder what would happen if we kept hooking up, but the relaxing power of her hands soothed me of any hesitations I might've had.

Instead I stood there, bent over, being milked by my 50-something year old boss, preparing for the best.

"So...so what do you want me to do to *gulp* train Allison?" I asked nervously.

"I will send you an e-mail every Monday morning with a description of your duties. And I expect you to complete them," she said. "Then I will want you to file a report back with me by Friday to make sure everything has been completed on time."

"You have six weeks to train this girl," Anne said. "Don't disappoint me. Or her."

She stood up on her toes and pulled my mouth into hers and kissed me passionately. "Now," Anne said. "Put yourself together. She'll be here in two hours."

****

As I settled down to my desk to check my e-mail I anxiously opened my outlook inbox to see what my "duties" for this week were.

Anne had sent me only one e-mail entitled "Duties." I clicked and waited what seemed lengthy seconds to view its contents. Inside I found attachments and a list of numbers of all the things I was supposed to do. It was rather boring - sorting paper, calling clients, and the, at number 8, was one word of Latinate origin: "fellatio."

"Oh, so this is how this nasty little game is going to work," I thought to myself. I tapped a quick message back to Anne to ask a follow-up question. "Give or receive?" I asked. I heard a little snicker from Anne's office followed by her reply on my screen.

"Receive"

****

As the clock ticked down to noon, I tried to do my best to subside my nervous energy by doing menial jobs, like organizing my e-mail address book, paying late bills, searching for new CDs I would be interesting in picking up.

If I was going to complete the assignment that Anne gave me I would have to be normal when I met Allison. I would have to be confident and not betray the slightest amount of desire to jump her bones and sputter cum all over her innocent co-ed face.

But the truth is I was dying to meet the girl I was supposed to lay, and so when I heard some commotion upstairs and some noise, I stood up and waited to meet my bride.

A crowd of ladies walked into our office from upstairs and automatically everybody stopped what they were doing and came over, I was kind of lost as they all started shaking hands, until Anne snapped me out of my loss for understanding and gestured towards a very dark and lithe young black woman in the center who had her hair done up in dread locks with coral shells and her body covered in earthen tones.

"Peter I want you to meet Allison Moffit," Anne said. I was dumb founded and instantly asexual.

"Hi" I muttered. "Hi" she said warmly letting her lengthy brown arm move towards me, seeking out a comrade-like handshake. We made eye contact, her dark brown eyes connecting with my green ones, her moist palm softly connecting with mine, and then disembarking from that connection.

I was still dumbfounded. I decided to take action. "My name is Peter and I am also an intern," I said. "So I think I have a good idea of how you feel. I've been here since the beginning of summer and I have decided to stay on as work study through the fall," I said, summoning all of my courage.

"Oh," she answered. I could tell she was a little nervous too. "Allison is a student in Chicago," explained Anne, quite professionally. "She decided to forego a busy internship in the city for one with us out here in the sticks," Anne went on.

"That's right, I was getting tired of all that concrete and brick," Allison said, raising her hands dramatically. "I wanted to be able to learn this trade in peaceful surroundings." She had a strange lilt in her voice, almost Caribbean, so I asked her if she was from Illinois.

"Oh, no" she gushed. "I'm from Trinidad." A flash of sudden anxiety hit me. How was I going to get this Nubian disciple of Bob Marley to go down on me? I rebounded from my selfish thought, but Anne certainly picked up my state of mind. She was proving to be more intuitive than I thought.

"Peter is going to train you," Anne said. "And I'll make sure that he stays on task," she said, winking at me. "Well," I thought to myself, "I'll do my best."

****

"Peter," Allison called out. It sounded more like "Peetah" the way she said it. "Could you come here, I need your help with something."

It had been three days training Allison, and things were going as well as they could. It felt odd being in this superior position, but Allison was willing to please, and although she was a little New Age-y in her appearance, she smelled delectable. She must have poured tons of lightly-fruit scented lotions over her apparently soft skin. I liked to just breathe her in when I had to come lean over her shoulders.

Although Allison wasn't exactly the pliable blonde co-ed I had imagined, she certainly was attractive, and...I know this sounds kind of obvious, but she was so dark. I'd never kissed a black girl before, but, despite my initial shock, I felt strangely drawn to her. She was supple in ways that many of the women I had dated, all of European backgrounds, weren't.

For one she had that infamous "booty" that so many adult sites and hip hop videos were constantly advertising. It sort of cleared the way for her whenever she walked anywhere, like a bridal gown, trailing behind her. Her bosoms were equally as supple, and they stuck out, warm and inviting, underneath her sunny colored dresses.

Sunny was a word that described the young lady from Trinidad well. In just a couple days we had developed a cordial flirtatious relationship. Though it was just starting. I already felt like I could make love to this woman, even if Anne had merely assigned "fellatio."

But how was I going to arrange that in one week? Ugh. It was so frustrating. I didn't want to screw it all up. After a day of wracking my brain, I finally approached Anne -- sheepishly -- for a little advice one afternoon a few days before my assignment was "due" in her office.

"So how is the training going?" Anne said coldly and wickedly.

"Um, it's fine Anne, but I am not sure how to proceed."

"Oh, I'm sure you can get her to do it, it's not that hard, you're a good looking guy."

"Yeah, but she's just a 19-year-old girl, from a different country," I responded.

"I bet you were surprised to meet Allison," Anne said, alluding to the tone of her skin.

"A little" I said, "but let's cut to the chase, I am at a loss for ideas."

"Ok fine," Anne said, taking a swig from a lukewarm coffee, leftover from that morning. "Barb and her husband Vincent are going out of town this weekend. They have a nice pool and a sauna. Why not invite Allison there?"

It seemed a bit reckless to go use Barb's stuff, but since Anne was tight with Barb, almost sisters, it seemed ok to take the idea up with Allison, or Alli as she liked to be called, at lunch.

"Thanks Anne," I said, you're a life saver. "What are bosses for?" she answered with a little grin.

**** "Hi Alli," I said to my trainee as she munched on her lunch of pasta salad on the front steps outside our office. "Mind if I joined you?"

"Sure thing, Petah," she said. I sat down and unbagged my lunch and got cozy.

"So are you enjoying the job?" I asked.

"I am enjoying your local culture," she smirked back. "I've seen a few fellows drive by in pickup trucks in the past few minutes."

"Well, that's what happens in these small towns," I answered. I wasn't from here either, and I knew the feeling of living on the rural outskirts of a big city for the first time.

"Have you made any friends here?" she asked.

"Well, it's not exactly easy to fit right in, but I've got a couple friends. Actually one of my friends is out for the weekend," I said, lying. "He's told me I've got to watch his house. It's a good gig because he's got a pool and a sauna."

I recoiled at how forthright I had been and for some reason shot a long glance at her ebony feet. Alli wrinkled her nose and looked me in the eyes, with a glare that could have sucked the paint off a pool ball.

"Now Peter," she said. "Are you stepping on me?"

I blushed. "Stepping on you?" I asked. "What does that mean?"

"Don't play games with me, Peter," she said. "I'm an island girl, and I have probably been hit on more times than you will ever be in your whole life!" she said.

"OK," I confessed. "I'm stepping on you."

"I KNEW it," she said with a big laugh. She then shoveled some more food in her mouth. "I've got big eyes, Peter," she said. "I've seen you checking out my ass." She elbowed me.

Now I cracked up laughing. "Yeah," I said. "That's also true."

"So tell me a little more about this pool and sauna," she said, drawing closer and taking my hand in hers. Everything felt sweet and innocent. Like she was my girlfriend.

"Describe it for me, because you are such a good trainer," she said laughing.

"Well," I gulped. "It's very, very hot."

"Oh, you are so creative!" she said back in her sly birdsong of a voice.

"And the pool is very, very cool."

"Sounds very inviting," she said.

"So," I continued. "Would you like to come up there with me this evening?"

"Oh Peter, I don't know if I can do that. I've just met you."

"Your loss," I said.

"Oh, OK fine," Alli responded, looking straight ahead and taking her hand away from mine. After another moment of thought she looked back at me. "I'll come out with you this evening."

****

We pulled up to Barb's house at around 11 pm that night after we had gone out to dinner. So far our physical contact had been light touching under the table at the restaurant we were at, but I could feel every vertebrate tickle as she peeled off her dress and revealed a light blue swimsuit that left little to the imagination.

She dove in head first into Barb's pool and as she looked up at me from the shallow end in the dark light I could honestly estimate that she was the most beautiful woman I had ever seen.

"Why are you staring at me like that, you fool?" she said. "Come on in. It's 'cool, very cool," she laughed.

I took off my shirt and dove in as well, feeling the immense wetness and coming up behind Alli.

As I looked into her eyes in the pool she started to hesitate. "Oh, Let's go use the sauna, OK?" she said.

We both climbed out of the pool and headed to the sauna to get warm. I started up the sauna's furnace and pretty soon we had a significant reading.

"So how does this work?" asked Alli. I gathered that she had never been in one of these things in her life.

"Well," I said. "The first thing you have to do is take your clothes off."

"NO!" she said laughing. "Really?" She wasn't being sarcastic.

"Yes, that's how it works," I answered.

"You first," she said playfully. I lowered my swim trunks nervously, slowly letting my penis hang out into the night air.

"Ooh," she said looking directly at it. "You ARE serious about this." She then undid her blue bikini top and let her majestic breasts tussle down. They were gorgeous, with dark brown areolae. I instantly wanted to suckle on them and squeeze them.

And then she took of the rest, revealing her tight, curly bush. I never felt so naked.

"Let's go in," I said.

We eased onto the hot benches next to one another, and she slowly placed her hand on my thigh. In the dark everything about her face became even more beautiful. Her eyes, her nose, her smooth brown skin. I leaned forward and we began a wet long kiss. She smelled so good and I breathed her in deep once again.

I began moving my torso closer to her, pulling her nearer. My penis filled with warm blood, and the sauna began to make the sweat bead off each of our backs.

There was something in the ether of our connection and we paused a minute as she looked into my eyes. "I want to suck you" she said timidly. "I want to drink you, Peter. I leaned back and she lowered her head into my lap. One of her dark hands gripped my balls, while the other guided my erect cock into her wet and deep mouth. The heat was becoming unbearable, and as she began warmly blowing me my whole body relaxed and my mind began to meander.

"Drink me" I said to Alli as I pumped my hips. "Drink all of me." "I want to drink you deep" she replied. Images raced through my head of this long legged girl and how good she was at giving head. Try as I may though I couldn't feel any sexual power over her though. I liked this girl, and so I decided to put down my fantasies of conquest and just relax. Each bob of her head drew my liquids closer and closer until I felt a strain in my cock and began to pump with enthusiasm, all the time she let out the cutest squeals you'd ever heard. She slurped and sucked away, plummeting on my organ until I began to cum, shooting healthy dollops of ejaculate in her mouth as she sucked harder, swallowing me deep, just like she had promised.

It was bitterly romantic. I let out a deep sigh. "Did you enjoy that? She asked playfully, her body slick with sweat.

"Yes," I gasped, pulling her closer. "Good she replied. Now let's get back in the pool. It is too hot in here. Too hot for more sex, and way to hot for a girl from Trinidad.